6,7-dichloro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one | 177980-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7-dichloro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6,7-dichloro-2-oxo-1H-imidazo[4,5-b]quinolin-4-yl)oxolan-2-yl]methyl benzoate
• CAS: 177980-39-1
• 化学式: C₃₆H₂₅Cl₂N₃O₈
• 分子量: 698.516
• InChiKey: NBFXHGLQTVTTDL-PBAMLIMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 6,7-dichloro-4-(β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
  参考文献：
  名称：

  6,7-二氯咪唑并[4,5 - b ]喹啉-2-酮的区域选择性核糖基化

  摘要：

  建立了区域选择性核糖基化条件，该条件可同时生成6,7-二氯-1-（2,3,5-三-O-苯甲酰基-β-D-核呋喃呋喃糖基）咪唑并[4,5 - b ]喹啉-2-酮（4）和6,7-二氯-3-（2,3,5-三- ø -苯甲酰-β-d-D-呋喃核糖基）咪唑并[4,5-b]喹啉-2-酮（5），分别在高由6，7-二氯咪唑并[4，5- b ]喹啉-2-酮（6）得到。讨论了在各种条件下核糖基化位点的分布。

  DOI：

  10.1016/0040-4039(96)00529-1
• 作为产物：
  描述：

  4,5-二氯-2-硝基苯胺 在 苯磺酰胺 、 ammonium hydroxide 、 sodium hydroxide 、 亚硝酸特丁酯 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 铁粉 、 copper(II) sulfate 、 iron(II) sulfate 、 溶剂黄146 、 三乙胺 、 pyridinium chlorochromate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 74.42h， 生成 6,7-dichloro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
  参考文献：
  名称：

  Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-b]quinolin-2-one

  摘要：

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.

  DOI：

  10.1021/jo982084o

文献信息

• Regioselective ribosylation of 6,7-dichloroimidazo[4,5-b]quinolin-2-one
  作者：Zhijian Zhu、Leroy B. Townsend

  DOI：10.1016/0040-4039(96)00529-1

  日期：1996.5

  Regioselective ribosylation conditions were established which gave both 6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one (4) and 6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo [4,5-b]quinolin-2-one (5), respectively, in high yield from 6,7-dichloroimidazo[4,5-b]quinolin-2-one (6). The distributions of the sites of ribosylation under a variety of conditions

  建立了区域选择性核糖基化条件，该条件可同时生成6,7-二氯-1-（2,3,5-三-O-苯甲酰基-β-D-核呋喃呋喃糖基）咪唑并[4,5 - b ]喹啉-2-酮（4）和6,7-二氯-3-（2,3,5-三- ø -苯甲酰-β-d-D-呋喃核糖基）咪唑并[4,5-b]喹啉-2-酮（5），分别在高由6，7-二氯咪唑并[4，5- b ]喹啉-2-酮（6）得到。讨论了在各种条件下核糖基化位点的分布。
• Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-<i>b</i>]quinolin-2-one
  作者：Zhijian Zhu、Blaise Lippa、Leroy B. Townsend

  DOI：10.1021/jo982084o

  日期：1999.5.1

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.